Can someone help me pick out my first speakers?

Big plus +1 for the Pioneer SP-BS22-LR. Eventually paired with one then two SVS subwoofers in your budget range should serve you nicely until you hit the Lotto.

I assembled two Pioneer BS22 7.1 HT systems for friends, one using two SVS SB-1000's and another with two Velodyne DD-10 Plus. Since they budgeted on the DD's they planned on upgrading the Pioneers. That was over two years ago.

While not in your budget my ownership with the then top of the line Paradigm Studio 100 v1, v2 and S8's I cannot recommended brand. 

There are some other good suggestions here you should take a hard look at.

Welcome to the Mob.

it's safe to say this is good value for $299 at 50% off

https://www.bestbuy.com/site/kef-q-series-5-25-2-way-bookshelf-speakers-pair-walnut/6379830.p?skuId=6379830&ref=212&loc=1&extStoreId=438&ref=212&loc=1&gclid=CjwKCAjw5P2aBhAlEiwAAdY7dMuaK6P84fqOW-vqUv1rFT5QJJMFgUpV2G_WmHre7AydgpuPNsU8hRoCcpgQAvD_BwE&gclsrc=aw.ds

There ya go! Op should jump on the KEF you linked unless good used deals around.

other thing to look at are the JBL studio stuff. While back they went on sale off and on and apparently sound pretty damn good. Pretty efficient so may sound ok with a crapper Receiever or whatever the OP has 

pair of Polk Audio Signature Elite ES20 over on usaudiomart for ~$300

The Triangle Br02 are $250 on Amazon right now.